Nosylaziridines: Activated aziridine electrophiles

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5253-5256

  Maligres, Peter E ^a   See, Marjorie M ^a   Askin, David ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZIRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ELECTRON; TECHNIQUE;

EID: 0030790051     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01157-X     Document Type: Article

References (29)

1. For monographs on aziridines see: Pearson, W.H.; Lian, B.W.; Bergmeier, S.C. Aziridines and Azirines: Monocyclic. in Comprehensive Heterocyclic Chemistry; Padwa, A., Ed. Pergamon Press; Oxford, 1996, Vol 1A and Padwa, A.; Woolhouse, A.D. Aziridines, Azirines, and Fused Ring Derivatives in Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed. Pergamon Press; Oxford, 1984, Vol 7.
2. For monographs on aziridines see: Pearson, W.H.; Lian, B.W.; Bergmeier, S.C. Aziridines and Azirines: Monocyclic. in Comprehensive Heterocyclic Chemistry; Padwa, A., Ed. Pergamon Press; Oxford, 1996, Vol 1A and Padwa, A.; Woolhouse, A.D. Aziridines, Azirines, and Fused Ring Derivatives in Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed. Pergamon Press; Oxford, 1984, Vol 7.
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15. To our knowledge there have been no reported cases of nosylaziridine openings by direct nucleophilic attack on the aziridine ring. A recent report of the opening of an allylic nosylaziridine via SN2' attack by an organocuprate has appeared: Wipf, P.; Henninger, T.C. J. Org. Chem. 1997, 62, 1586-1587.
16. (a) Isaacs, N.S. Physical Organic Chemistry, Longman Scientific & Technical, Essex, 1987, p. 453-462.
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21. -1). Similar results for the reactivity difference between 1 and the corresponding tosylaziridine were obtained with benzylamine and benzyl mercaptan as nucleophiles.
22. 3) δ 150.6, 144.2, 129.1, 124.3, 36.8, 35.5, 16.8.
23. 3) δ 149.9, 147.2, 128.2, 124.1, 75.5, 58.7, 49.5, 18.2.
24. 3) δ 150.6, 143.9, 134.2, 129.2, 128.8, 126.5, 124.4, 41.9, 36.6.
25. 2 at 300 bar over 28 min, 1 mL/min flow at 35°C with detection at 220 nm, retention times: (S)-2 = 16.6 min, (R)-2 = 18.3 min, 8i antipodes = 20.4, 23.4 min. The absolute configuration of the product 8i has not been determined.
26. Fukuyama, T.; Jow, C-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373-6374.
27. 3) δ 155.4, 79.1, 75.8, 59.0, 46.0, 28.4, 17.9.
28. 2-MTBE-hexane (20 mL) to provide (rac)-2 as a white crystalline solid (858 mg, 56% yield). The preparation of PhI=NNs was similar to that described in the literature: (a) Besenyei, G.; Nemeth, S.; Simandi, L.I. Tetrahedron Lett. 1993, 34, 6105-6106.
29. (b) Yamada, Y.; Yamamoto, T.; Okawara, M. Chem. Lett. 1975, 361-362.